CA1268473A - Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals - Google Patents

Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals

Info

Publication number
CA1268473A
CA1268473A CA000445903A CA445903A CA1268473A CA 1268473 A CA1268473 A CA 1268473A CA 000445903 A CA000445903 A CA 000445903A CA 445903 A CA445903 A CA 445903A CA 1268473 A CA1268473 A CA 1268473A
Authority
CA
Canada
Prior art keywords
hydrogen
compound
benzyloxy
chloro
fluoro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA000445903A
Other languages
English (en)
French (fr)
Inventor
Paul L. Anderson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz AG filed Critical Sandoz AG
Application granted granted Critical
Publication of CA1268473A publication Critical patent/CA1268473A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34Halogenated alcohols
    • C07C31/38Halogenated alcohols containing only fluorine as halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/202Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a naphthalene
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/42Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56Unsaturated compounds containing hydroxy or O-metal groups containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30Oxygen atoms, e.g. delta-lactones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Confectionery (AREA)
  • Pyrane Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Furan Compounds (AREA)
CA000445903A 1983-01-24 1984-01-23 Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals Expired - Lifetime CA1268473A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46060083A 1983-01-24 1983-01-24
US460,600 1983-01-24

Publications (1)

Publication Number Publication Date
CA1268473A true CA1268473A (en) 1990-05-01

Family

ID=23829363

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000445903A Expired - Lifetime CA1268473A (en) 1983-01-24 1984-01-23 Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals

Country Status (19)

Country Link
EP (1) EP0117228B1 (de)
JP (1) JPS60500499A (de)
KR (1) KR840007555A (de)
AT (1) ATE23326T1 (de)
AU (1) AU570942B2 (de)
CA (1) CA1268473A (de)
DE (1) DE3461180D1 (de)
DK (1) DK454184A (de)
ES (1) ES8609193A1 (de)
FI (1) FI843560L (de)
GR (1) GR81711B (de)
HU (1) HU199769B (de)
IE (1) IE840153L (de)
IL (1) IL70767A (de)
NZ (1) NZ206919A (de)
PL (1) PL144594B1 (de)
PT (1) PT77996B (de)
WO (1) WO1984002903A1 (de)
ZA (1) ZA84547B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613610A (en) * 1984-06-22 1986-09-23 Sandoz Pharmaceuticals Corp. Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives
KR910003427B1 (ko) * 1984-12-04 1991-05-31 산도즈 파마슈티칼스 코포레이션 메발로노락톤의 인덴동족체 및 이들의 유도체의 제법
US5001255A (en) * 1984-12-04 1991-03-19 Sandoz Pharm. Corp. Idene analogs of mevalonolactone and derivatives thereof
US4668794A (en) * 1985-05-22 1987-05-26 Sandoz Pharm. Corp. Intermediate imidazole acrolein analogs
US4851427A (en) * 1985-10-25 1989-07-25 Sandoz Pharm. Corp. Pyrrole analogs of mevalonolactone, derivatives thereof and pharmaceutical use
KR900001212B1 (ko) * 1985-10-25 1990-02-28 산도즈 파마슈티칼스 코오포레이숀 메바로노락톤 및 그것의 유도체의 헤테로사이클릭 유사체 및 그것의 생산방법 및 약학적인 그것의 용도
ZW10287A1 (en) * 1986-07-15 1988-01-13 Hoffmann La Roche Tetrahydronaphthaline and indane derivatives
NZ221717A (en) * 1986-09-10 1990-08-28 Sandoz Ltd Azaindole and indolizine derivatives and pharmaceutical compositions
US4751235A (en) * 1986-12-23 1988-06-14 Sandoz Pharm. Corp. Anti-atherosclerotic indolizine derivatives
US4898949A (en) * 1987-02-25 1990-02-06 Bristol-Myers Company Intermediates for the preparation of antihypercholesterolemic tetrazole compounds
US4897490A (en) * 1987-02-25 1990-01-30 Bristol-Meyers Company Antihypercholesterolemic tetrazole compounds
US4904646A (en) * 1987-05-22 1990-02-27 E. R. Squibb & Sons, Inc. Phosphorus-containing HMG-COA reductase inhibitors
US5091378A (en) * 1987-05-22 1992-02-25 E. R. Squibb & Sons, Inc. Phosphorus-containing HMG-CoA reductase inhibitors, new intermediates and method
US5010205A (en) * 1988-08-23 1991-04-23 Bristol-Myers Company Antihypercholesterolemic tetrazol-1-yl intermediates
US5506219A (en) * 1988-08-29 1996-04-09 E. R. Squibb & Sons, Inc. Pyridine anchors for HMG-CoA reductase inhibitors
WO2006123355A2 (en) * 2004-11-03 2006-11-23 Sun Pharmaceutical Industries Limited Novel statin derivatives
JP6024259B2 (ja) * 2011-07-25 2016-11-16 東ソー株式会社 新規なナフタルアルデヒド化合物、その製造法、および該化合物からトリアリールアミン化合物を製造する方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5559140A (en) * 1978-10-30 1980-05-02 Sankyo Co Ltd 3,5-dihydroxypentanoic alkyl ester derivative, its preparation and remedy for hyperlipemia containing the same as the effective component
AU548996B2 (en) * 1980-02-04 1986-01-09 Merck & Co., Inc. Tetrahydro-2h-pyran-2-one derivatives

Also Published As

Publication number Publication date
ZA84547B (en) 1985-09-25
IE840153L (en) 1984-07-24
GR81711B (de) 1984-12-12
ES8609193A1 (es) 1986-07-16
KR840007555A (ko) 1984-12-08
DK454184D0 (da) 1984-09-21
IL70767A0 (en) 1984-04-30
HUT37380A (en) 1985-12-28
AU2433184A (en) 1984-08-15
PL144594B1 (en) 1988-06-30
JPS60500499A (ja) 1985-04-11
AU570942B2 (en) 1988-03-31
EP0117228B1 (de) 1986-11-05
HU199769B (en) 1990-03-28
WO1984002903A1 (en) 1984-08-02
FI843560A0 (fi) 1984-09-11
EP0117228A1 (de) 1984-08-29
NZ206919A (en) 1987-08-31
ES529090A0 (es) 1986-07-16
DK454184A (da) 1984-09-21
PL245886A1 (en) 1985-12-03
ATE23326T1 (de) 1986-11-15
IL70767A (en) 1988-06-30
DE3461180D1 (en) 1986-12-11
PT77996B (en) 1986-05-30
FI843560L (fi) 1984-09-11
PT77996A (en) 1984-02-01

Similar Documents

Publication Publication Date Title
CA1268473A (en) Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals
CA1210405A (en) Analogs of mevalolactone and derivatives thereof
US4668794A (en) Intermediate imidazole acrolein analogs
US4686237A (en) Erythro-(E)-7-[3'-C1-3 alkyl-1'-(3",5"-dimethylphenyl)naphth-2'-yl]-3,5-dihydroxyhept-6-enoic acids and derivatives thereof
US4613610A (en) Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives
KR900009006B1 (ko) 메발로락톤의 동족체 및 그것의 유도체의 제조방법
US4950767A (en) Process for the preparation of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene
US4645854A (en) Process for preparing HMG-CoA reductase inhibitors with a 3,5-dihydroxypentanoate subunit
US5693816A (en) Process for the preparation of diisopinocampheylchloroborane
US4755606A (en) Imidazolyl-3,5-di-(diphenyl-butylsilyloxy) carboxylic acid ester intermediates
EP0000035A1 (de) Alpha-Aminosäuren, Präparate und Verfahren zur Herstellung dieser Verbindungen
US5412134A (en) Process for preparing diprotected 2,3-hydroxymethyl cyclobutanol
US5208258A (en) Antihypercholesterolemic compounds and synthesis thereof
US4804679A (en) Erythro-(E)-7-(3'-C1-3alkyl-1'-(3",5"-dimethylphenyl)naphth-2'-yl)-3,5-dihydroxyhept-6-enoic acids and derivatives thereof
US4950775A (en) Antihypercholesterolemic compounds and synthesis thereof
US5543526A (en) 1-amino-4-(1H-imidazole)- aminobutaneboronic acid derivatives, their preparation and use as synthetic intermediates
CS226740B2 (en) Method of preparing (7e,9z)-alkadienol derivatives
CA1326675C (fr) Derives trieniques de structure chromenique, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
US5001255A (en) Idene analogs of mevalonolactone and derivatives thereof
US4360694A (en) Process for preparing 1,2-diacyl-sn-glycerols
US4487957A (en) Process for the preparation of alkyl 4-methyl-3-formyl-penten-1-oates
US4661641A (en) Substituted alkynes useful as intermediates in the synthesis of carotenoids
JPH01503196A (ja) 光学的活性化合物
US4322557A (en) 1-Aryloxy-2-(S)-hydroxy-3-(triarylphosphonio)-propane derivatives as prostaglandin intermediates
US4900476A (en) Quinone intermediates for asymmetric synthesis of natural vitamin E

Legal Events

Date Code Title Description
MKLA Lapsed